CN110003411B - Preparation method of polycondensation macromolecule photoinitiator and prepared photoinitiator - Google Patents
Preparation method of polycondensation macromolecule photoinitiator and prepared photoinitiator Download PDFInfo
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- 238000006068 polycondensation reaction Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 229920002521 macromolecule Polymers 0.000 title claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000013078 crystal Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 150000002576 ketones Chemical class 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000000178 monomer Substances 0.000 claims abstract description 9
- 229920001744 Polyaldehyde Polymers 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229960001701 chloroform Drugs 0.000 claims description 8
- 229910052711 selenium Inorganic materials 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 238000000016 photochemical curing Methods 0.000 claims 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 1
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- 239000003999 initiator Substances 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000002202 Polyethylene glycol Substances 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 229920001223 polyethylene glycol Polymers 0.000 abstract description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- HJULPPMMCXMWJA-UHFFFAOYSA-N 1-(5-acetylfuran-2-yl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)O1 HJULPPMMCXMWJA-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910006069 SO3H Inorganic materials 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 229910000144 sodium(I) superoxide Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012536 packaging technology Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G6/00—Condensation polymers of aldehydes or ketones only
- C08G6/02—Condensation polymers of aldehydes or ketones only of aldehydes with ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of a polycondensation macromolecular photoinitiator, which relates to the technical field of synthesis of photoinitiators in the field of photopolymerization and comprises the following steps: mixing alpha-H-free polyaldehyde with alpha-H-containing ketone or acetyl-containing compound, adding a solvent, adding 1-25% by mass of an alkali solution, introducing nitrogen for reaction, reacting at 20-50 ℃ for 1-24H, carrying out ice bath for 1-10H to precipitate crystals, washing with an organic solvent, and removing the solvent to obtain a product. The invention has the beneficial effects that: the preparation method has simple conditions, mild reaction and easy purification of the product; the prepared photoinitiator and polyethylene glycol monomer have high reaction rate under the condition of not adding an auxiliary initiator, and the conversion rate of double bonds in 300s can reach about 90%.
Description
Technical Field
The invention relates to the technical field of synthesis of photoinitiators in the field of photopolymerization, and particularly relates to a polycondensation macromolecular photoinitiator and a preparation method thereof.
Background
In a photocurable system, a photo-initiator, upon absorption of suitable light energy, undergoes a photophysical process to an excited state, where the energy is greater than the energy required for bond cleavage, and can generate primary reactive species, such as radicals or ions, to initiate polymerization. As the photoinitiator, it is generally required to satisfy the following conditions: (1) the quantum efficiency of the initiation is high; (2) the range of the absorption spectrum is matched with the irradiation light source; (3) the thermal stability is good, and no dark reaction exists; (4) has better compatibility with monomers and prepolymers.
The traditional mercury lamp light source is gradually prohibited from being used due to high pollution, and is replaced by an LED light source, and the preparation technology of the LED light source with short wavelength is limited by packaging technology and materials, so that the design and synthesis of the photoinitiator adaptive to the LED light source are the development trend of the photopolymerization technology.
Disclosure of Invention
The technical problem solved by the invention is that the traditional photoinitiator is limited by the wavelength of an LED light source.
The invention adopts the following technical scheme to solve the technical problems:
a preparation method of a polycondensation macromolecular photoinitiator comprises the following steps:
mixing alpha-H-free polyaldehyde with alpha-H-containing ketone or acetyl-containing compound, adding a solvent, adding 1-25% by mass of an alkali solution, introducing nitrogen for reaction, reacting at 20-50 ℃ for 1-24H, carrying out ice bath for 1-10H to precipitate crystals, washing with an organic solvent, and removing the solvent to obtain the product.
Preferably, the alpha-H free polyaldehydes have the general structural formula:
wherein X is O, S, N, C or Se; when X is O, S or Se, no R1、R5、R7；
In other cases: (1) r1-R7Is H or a halogen substituent: -F, -Cl, -Br, -I; or a substituent with O: -CHO, -COOH, -CO, -OH; or a substituent bearing N: -NH3、-NO2-CN; or a substituent with S: -HS, -SO3H、-CH2S; or alkane, alkene, alkyne and arene whole chain or branched chain with the substituent groups;
(2) the substituents not related to (1) are summarized as follows: r1-R7is-NaO2S、-B(OH)2、
Wherein h is 1-12; x is the element described in (1); r34-R37The substituents described in (1) and (2).
Preferably, the structural formula of the alpha-H containing ketone or acetyl group containing compound is as follows:
wherein Y is O, S, N or C; w is C, N, O, S, P, Si or Se; m, n, J, k are 1, 2, 3, 4, 5 or 6; when W is O, S or Se, no R13、R17、R18、R24；
In other cases: r8-R25Is H or a halogen substituent: -F, -Cl, -Br, -I; or a substituent with O: -CHO, -COOH, -CO, -OH; or a substituent bearing N: -NH3、-NO2-CN; or a substituent with S: -HS, -SO3H、-CH2S; or alkane, alkene, alkyne and arene whole chain or branched chain with the substituent groups;
(2) the substituents not related to (1) are summarized as follows: r8-R25is-NaO2S、-B(OH)2、
Wherein h is 1-12; x is the element described in (1); r34-R37The substituents described in (1) and (2).
Preferably, the polyaldehydes without alpha-H have the general structural formula
The structural general formula of the ketone containing alpha-H is
When the general structural formula of the product is
Wherein i is a positive integer.
In other cases: r1、R2、R3、R8、R9Is composed of
Preferably, the polyaldehydes without alpha-H have the general structural formula
The structural general formula of the ketone containing alpha-H is
When the general structural formula of the product is
Wherein l is a positive integer.
Preferably, the solvent is one or more of ethanol, ethyl acetate, chloroform and acetonitrile.
Preferably, the alkali solution is ammonia, sodium hydroxide, potassium hydroxide or sodium bicarbonate.
Preferably, the organic solvent is methanol, ethanol, ethyl acetate, dichloromethane, chloroform, acetonitrile or acetone.
The invention also provides a polycondensation macromolecular photoinitiator prepared by the preparation method.
The invention has the beneficial effects that:
(1) the preparation method has simple conditions and mild reaction, and the product is easy to purify;
(2) the condensed photoinitiator has O, S, N and Se atoms on a hybrid five-membered ring structure and has isolated electric pairs, can form a large conjugated system with a double-bond structure, and the conjugated structure is continuously and prolonged by polycondensation, so that the maximum absorption wavelength of the photoinitiator reaches more than 600nm due to the increase of the conjugation degree;
(3) under the condition that the photoinitiator and the polyethylene glycol monomer are not added with the auxiliary initiator, the reaction rate is high, the conversion rate of double bonds in 300s can reach about 90 percent, the content of the photoinitiator only reaches 0.01 percent of the mass of the monomer, and the photoinitiator has the photobleaching effect, low toxicity and low migration;
(4) the longer the absorption wavelength of the photoinitiator, the longer the wavelength of the light source required for initiation, the less energy required in the photoinitiation process, the less energy consumption and the more environment-friendly;
(5) the molecular weight of the product can be controlled by adjusting the reaction conditions, and the different molecular weights of the products mean different conjugation degrees in the structure of the product and different light absorption wavelengths, so that a series of photoinitiators with gradient absorption wavelengths are obtained by reaction and can be matched with different light sources for use.
Detailed Description
The present invention will be described in detail with reference to preferred embodiments thereof for the purpose of providing a better understanding and appreciation for the structural features and advantages achieved thereby.
In the present invention, the components and raw materials are all conventional commercially available products or can be obtained by means of conventional techniques in the art.
Example 1
A preparation method of a polycondensation macromolecular photoinitiator comprises the following steps:
(1) weighing 1mol of 2, 5-aldehyde furan and 1mol of cyclohexanone, dissolving in 20mL of ethyl acetate, and uniformly mixing under stirring;
(2) dropwise adding 3-5 drops of 5% by mass NaOH aqueous solution (0.5g of NaOH and 9.5g of water) into the mixed solution prepared in the step (1), adjusting the pH value to 13, reacting at 30 ℃ for 3 hours, introducing nitrogen, continuously reacting for 3 hours by using an ice bath, and separating out light yellow crystals;
(3) the light yellow crystals from step (2) were washed with dichloromethane and dried under vacuum to remove the solvent to give pure light yellow product.
The properties of the initiator prepared in this example were tested as follows: the product of example 1 was used at 1X 10-5Is dissolved in acetonitrileIn (c), the ultraviolet absorption was tested.
The experimental results are as follows: the absorption wavelength range is 250nm-425nm, and the maximum absorption peak is 375 nm.
Example 2
A preparation method of a polycondensation macromolecular photoinitiator comprises the following steps:
(1) weighing 1mol of 2, 5-aldehyde furan and 1mol of cyclohexanone, dissolving in 20mL of ethanol/ethyl acetate (volume ratio is 20%/80%), and uniformly mixing under stirring;
(2) dropwise adding 3-5 drops of 5% by mass NaOH aqueous solution (0.5g of NaOH and 9.5g of water) into the mixed solution prepared in the step (1), adjusting the pH value to 13, reacting at 30 ℃ for 3 hours, introducing nitrogen, continuously reacting for 3 hours by using an ice bath, and separating out light yellow crystals;
(3) the light yellow crystals obtained in step (2) were washed with dichloromethane and dried under vacuum to remove the solvent to give pure light yellow product.
The properties of the initiator prepared in this example were tested as follows: the product of example 2 was used at 1X 10-5Was dissolved in acetonitrile and tested for uv absorption.
The experimental results are as follows: the absorption wavelength range is 250nm-460nm, and the maximum absorption peak is at 395 nm.
Example 3
A preparation method of a polycondensation macromolecular photoinitiator comprises the following steps:
(1) weighing 1mol of 2, 5-aldehyde furan and 1mol of cyclohexanone, dissolving in 20mL of trichloromethane, and uniformly mixing under stirring;
(2) dropwise adding 3-5 drops of 5% by mass NaOH aqueous solution (0.5g of NaOH and 9.5g of water) into the mixed solution prepared in the step (1), adjusting the pH value to 13, reacting at 30 ℃ for 3 hours, introducing nitrogen, continuously reacting for 3 hours by using an ice bath, and separating out light yellow crystals;
(3) and (3) washing the light yellow crystals obtained in the step (2) by using trichloromethane, and drying in vacuum to remove the solvent to obtain a pure light yellow product.
The properties of the initiator prepared in this example were tested as follows: the product of example 3 was purified by1×10-5Was dissolved in acetonitrile and tested for uv absorption.
The experimental results are as follows: the absorption wavelength range is 250nm-500nm, and the maximum absorption peak is at 420 nm.
Example 4
A preparation method of a polycondensation macromolecular photoinitiator comprises the following steps:
(1) weighing 1mol of 2, 5-aldehyde furan and 1mol of 2, 5-diacetyl furan, dissolving in 20mL of ethanol, and uniformly mixing under stirring;
(2) dropwise adding 3-5 drops of 5% by mass NaOH aqueous solution (0.5g of NaOH and 9.5g of water) into the mixed solution prepared in the step (1), adjusting the pH value to 13, reacting at 30 ℃ for 3 hours, introducing nitrogen, continuously reacting for 3 hours by using an ice bath, and separating out light yellow crystals;
(3) the light yellow crystals obtained in step (2) were washed with dichloromethane and dried under vacuum to remove the solvent to give pure light yellow product.
Example 5
A preparation method of a polycondensation macromolecular photoinitiator comprises the following steps:
(1) weighing 1mol of 2, 5-aldehyde furan and 1mol of 2, 5-diacetyl furan, dissolving in 20mL of ethyl acetate, and uniformly mixing under stirring;
(2) dropwise adding 3-5 drops of 5% by mass NaOH aqueous solution (0.5g of NaOH and 9.5g of water) into the mixed solution prepared in the step (1), adjusting the pH value to 13, reacting at 30 ℃ for 3 hours, introducing nitrogen, continuously reacting for 3 hours by using an ice bath, and separating out light yellow crystals;
(3) and (3) washing the light yellow crystals obtained in the step (2) by using a dichloromethane mixed solvent, and removing the solvent by vacuum drying to obtain a pure light yellow product.
Example 6
A preparation method of a polycondensation macromolecular photoinitiator comprises the following steps:
(1) weighing 1mol of 2, 5-aldehyde furan and 1mol of 2, 5-diacetyl furan, dissolving in 20mL of trichloromethane, and uniformly mixing under stirring;
(2) and (2) dropwise adding 3-5 drops of 5% by mass NaOH aqueous solution (0.5g of NaOH and 9.5g of water) into the mixed solution prepared in the step (1), adjusting the pH value to 13, reacting at 30 ℃ for 3 hours, introducing nitrogen, and continuing to react for 3 hours by using an ice bath to precipitate light yellow crystals.
(3) And (3) washing the light yellow crystals obtained in the step (2) by using trichloromethane, and drying in vacuum to remove the solvent to obtain a pure light yellow product.
Example 7
The products of examples 1, 2 and 3 were added to HEA monomer in an amount of 0.01% by mass, and labeled sample 1, sample 2 and sample 3 were respectively placed in 10mL centrifuge tubes, and irradiated with 385nm LED light for 15 minutes, and all of sample 1, sample 2 and sample 3 were cured to touch dry.
Example 8
The general structural formula of the aldehyde which does not correspond to the absence of alpha-H is summarized below:
example 9
The structural general formula of the alpha-H containing ketone substance or diacetyl substance which does not conform to the above structural general formula is summarized as follows:
the above is only a preferred embodiment of the present invention, the protection scope of the present invention is not limited to the above examples, and various process schemes which are not different from the concept of the present invention are within the protection scope of the present invention.
Claims (4)
1. The application of the polycondensation macromolecular photoinitiator in the photocuring reaction of the HEA monomer is characterized in that: the preparation method of the polycondensation macromolecule comprises the following steps: mixing alpha-H-free polyaldehyde with alpha-H-containing ketone, adding a solvent, adding 1-25% by mass of an alkali solution, introducing nitrogen for reaction, reacting at 20-50 ℃ for 1-24H, performing ice bath for 1-10H to precipitate crystals, washing with an organic solvent, and removing the solvent to obtain a product;
the alpha-H-free polyaldehyde has the following structural general formula:
wherein X is O, S or Se; r2-R3Is H or a halogen substituent: -F, -Cl, -Br, -I;
the structural general formula of the alpha-H containing ketone is as follows:
2. Use of a polycondensation macromolecular photoinitiator according to claim 1 for the photocuring of HEA monomers, characterized in that: the solvent is one or more of ethanol, ethyl acetate, chloroform and acetonitrile.
3. Use of a polycondensation macromolecular photoinitiator according to claim 1 for the photocuring of HEA monomers, characterized in that: the alkali solution is the solution of ammonia water, sodium hydroxide, potassium hydroxide or sodium bicarbonate.
4. Use of a polycondensation macromolecular photoinitiator according to claim 1 for the photocuring of HEA monomers, characterized in that: the organic solvent is methanol, ethanol, ethyl acetate, dichloromethane, trichloromethane, acetonitrile or acetone.
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| CN101003608A (en) * | 2006-01-03 | 2007-07-25 | 德古萨公司 | Resins containing ionic liquids |
| JP2014009325A (en) * | 2012-07-02 | 2014-01-20 | Nippon Kagaku Kogyosho:Kk | Novel photopolymerization initiator and photosensitive resin composition using the same |
| CN108558794A (en) * | 2018-05-17 | 2018-09-21 | 北京化工大学 | A kind of preparation method for reacting synthesis light-sensitive compound according to Claisen-Schmidt |
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